CN107090299A - A kind of liquid-crystal composition of substituted compound of polyfluoro containing methyl substituents and its application - Google Patents

A kind of liquid-crystal composition of substituted compound of polyfluoro containing methyl substituents and its application Download PDF

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CN107090299A
CN107090299A CN201710397961.4A CN201710397961A CN107090299A CN 107090299 A CN107090299 A CN 107090299A CN 201710397961 A CN201710397961 A CN 201710397961A CN 107090299 A CN107090299 A CN 107090299A
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crystal composition
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CN107090299B (en
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史子谦
丰佩川
尹环
于涛
董向波
孙燕
付博
房凤梅
马峰
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Yantai Xianhua Technology Group Co ltd
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Abstract

The present invention relates to a kind of liquid-crystal composition of the substituted compound of polyfluoro containing methyl substituents, including the compound represented by one or more formulas I:

Description

A kind of liquid-crystal composition of substituted compound of polyfluoro containing methyl substituents and its application
Technical field
The present invention relates to the liquid crystal of a kind of liquid-crystal composition, more particularly to a kind of polyfluoro containing methyl substituents substituted compound Composition, belongs to liquid crystal display material technical field.
Background technology
Liquid crystal material is the key raw material for realizing liquid crystal display, in the world, the mixed liquor for TFT-LCD Brilliant material is monopolized by German Merck companies and Chisso companies of Japan, be the characteristics of China's liquid crystal material industry TN (distort to Row), STN (super twisted nematic) is relatively strong and TFT is very weak, liquid crystal monomer, intermediate are relatively strong and mixed liquid crystal is weaker.To downstream manufacturers For, required for liquid crystal panel production is all mixed liquid crystal material, and TFT-LCD is also occupied already in field of liquid crystal Leading position, therefore, the production domesticization of TFT mixed liquid crystals are the important steps that FPD industry improves domestic adaptive capacity for imported equipment.
Liquid crystal material passes through the development of more than 30 years, and 10,000 plurality of liquid crystals monomers have been synthesized at present, wherein conventional liquid crystal Display material has thousands of kinds, is classified by the center bridged bond of liquid crystal molecule and the feature of ring, mainly there is biphenyl liquid crystal, benzyl ring Hexane liquid crystal, ester liquid crystal, alkyne type liquid crystal, difluoromethoxy bridge liquid crystal, ethane and heterocyclic etc..
The liquid crystal material in TFT-LCD can be used except requiring that physical parameter matches with device, such as dielectric is each to different Property, refractive anisotrop, elastic constant also requires high stability, including ultraviolet light stability, high-temperature stability and change in addition Learn stability etc..There can be the liquid crystal material of high stability, polar group can only be the liquid crystal of F substitutions.Due to single liquid Brilliant material can not possibly reach that various aspects of performance is all excellent, so exploitation mixed liquid crystal material, is mixed with the monocrystalline of different structure After conjunction, reach that each side index is as excellent as possible.
The content of the invention
The present invention takes for deficiency present on existing single liquid crystal material property there is provided a kind of polyfluoro containing methyl substituents Liquid-crystal composition and its application for compound.
The technical scheme that the present invention solves above-mentioned technical problem is as follows:
A kind of liquid-crystal composition of the substituted compound of polyfluoro containing methyl substituents, it is characterised in that including one or more Compound represented by formula I:
Wherein, R represents that alkoxy or carbon number that alkyl, carbon number that carbon number is 1-7 are 1-6 are 2-6's Institute's shape after one or more hydrogen are replaced by fluorine in the alkyl that alkenyloxy group that alkenyl, carbon number are 3-5, carbon number are 1-7 Into group, the group, the carbon number that are formed are after carbon number is replaced by one or more hydrogen in 1-6 alkoxy by fluorine Any one in the group that one or more hydrogen are formed after being replaced by fluorine in 3-5 alkenyloxy group;
L1, L2, L3Respective independent expression H or F;
X0Represent that haloalkyl, carbon number that alkyl, carbon number that F, Cl, carbon number are 1-6 are 1-6 are 2-6 Alkylene, carbon number be 2-6 haloalkene alkyl, carbon number be 1-6 halogenated alkoxy or carbon number be 2-6's Any one in halo alkenyloxy group;
One or more in independent expression following groups:
M represents 1,2.
Further, the structural formula of the compound with formula I is as follows:
Further, in addition to the compound as represented by formula II~IV:
In formula II-IV, R1-R4Alkyl that each independent expression hydrogen atom, carbon number are 1-7, carbon number are 1- In the alkyl that alkenyloxy group that alkenyl that 6 alkoxy or carbon number is 2-6, carbon number are 3-5, carbon number are 1-7 Group that one or more hydrogen are formed after being replaced by fluorine, carbon number are taken for one or more hydrogen in 1-6 alkoxy by fluorine In the group that group, the carbon number formed after generation is formed after being replaced by one or more hydrogen in 3-5 alkenyloxy group by fluorine Any one;
L1-L9Respective independent expression H or F;
X1、X2Represent that haloalkyl, carbon number that alkyl, carbon number that F, Cl, carbon number are 1-6 are 1-6 are 1- Haloalkene alkyl that alkylene that 6 halogenated alkoxy, carbon number are 2-6, carbon number are 2-6, carbon number are 2-6's Any one in halo alkenyloxy group;
Respective any one or more independent represented in following group:
Z1Represent singly-bound ,-CH2-、-CH2-CH2- ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、-OCH2-、- CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4- in one kind;
A, b, c, d, e, f, g represent 0,1 or 2.
Further, the structural formula of compound with formula II is as follows:
Wherein, R1、R2The alkoxy that alkyl that independent expression H atom, carbon number are 1~7, carbon number are 1~6 Or carbon number be 2~6 alkenyl, carbon number be 3~5 alkenyloxy group in any one.
Further, the structural formula of compound with general formula III is as follows:
Wherein, R3Represent alkoxy or carbon atom that alkyl, carbon number that H atom, carbon number are 1~7 are 1~6 Any one in the alkenyloxy group that alkenyl that number is 2~6, carbon number are 3~5.
Further, the structural formula of compound with general formulae IV is as follows:
Wherein, R4Represent alkoxy or carbon atom that alkyl, carbon number that H atom, carbon number are 1~7 are 1~6 Any one in the alkenyloxy group that alkenyl that number is 2~6, carbon number are 3~5.
Further, fraction meter by weight, compounds contents of the one or more with formula I are 1~40%, a kind of or many It is 1~70% to plant the compounds content with formula II, and compounds of the one or more with general formula III are 1~70%, a kind of Or a variety of compounds with general formulae IV are 1~50%.
The beneficial effects of the invention are as follows:
The liquid-crystal composition that the present invention is obtained has the operating temperature of non-constant width, relatively low threshold voltage, high resistivity And voltage retention, by force, good UV performances are ultraviolet front and rear all with high electric charge conservation rate, ion concentration for chemical stability Change after ultraviolet light smaller.Therefore suitable for the TFT LCDs of TN, IPS, FFS isotype.
Electrooptics liquid crystal display and above-mentioned liquid-crystal composition containing above-mentioned liquid-crystal composition is also claimed in the present invention In the application of field of liquid crystal display.
The liquid-crystal composition of the present invention can be produced two or more liquid-crystal compounds mixing using conventional method, such as Mixing different component and method preparation soluble in one another at high temperature, wherein, liquid-crystal composition is dissolved in for the compound Solvent in and mix, the solvent is then distilled out under reduced pressure;Or the liquid-crystal composition of the present invention can be according to conventional side Prepared by method, such as the less component of wherein content is dissolved in the larger key component of content at a higher temperature, or will be each Affiliated component dissolves in organic solvent, such as acetone, chloroform or methanol, is obtained after removing solvent after then solution is mixed.
Embodiment
The principle and feature of the present invention are described below in conjunction with example, the given examples are served only to explain the present invention, and It is non-to be used to limit the scope of the present invention.
The liquid-crystal composition of gained is used first using the heat of solution or concussion mixed method that generally use in the industry in embodiment Balance weighs liquid-crystal compounds by weight percentage, wherein addition sequence is weighed without particular requirement, it is generally molten with liquid-crystal compounds The order of point from high to low weighs mixing successively, is shaken under 60 DEG C of constant temperature in heating stirring or earthquake machine so that each component melts Solution is uniform, then produces target sample through absorption, the filter of micro-filtration membrane microfiltration, finally encapsulation.
Percentage in embodiment is weight percentage, and temperature is degree Celsius (DEG C).Such as illustrate without other, other symbols Specific meaning and test condition are as follows:
Cp (DEG C) represents the clearing point of liquid crystal.
S-N represents the crystalline state of liquid crystal to nematic fusing point (DEG C).
△ n are optical anisotropy, and no is the refractive index of ordinary light, and ne is the refractive index of extraordinary ray, and test condition is, 589nm wavelength, 25 DEG C.Measuring instrument:Abbe refractometer
△ ε are dielectric anisotropy, △ ε=ε ∥-ε ⊥, wherein, ε ∥ are the dielectric constant parallel to molecular axis, and ε ⊥ are Perpendicular to the dielectric constant of molecular axis, test condition is 25 DEG C;Measuring instrument:INSTEC:ALCT-IR1;20 microns of parallel boxes, It is not added with chiral agent.
γ1:Rotary viscosity (mPas), test condition is 25 ± 0.2 DEG C.
Measuring instrument:INSTEC:ALCT-IR1;20 microns of parallel boxes, are not added with chiral agent.
Embodiment 1:
The formula of liquid-crystal composition is as follows:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1
Numerical value ≤-40 88 0.110 1.598 5.0 3.3 63
Embodiment 2:
The formula of liquid-crystal composition is as follows:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1
Numerical value ≤-30 100 0.110 1.586 7.6 3.4 105
Embodiment 3:
The formula of liquid-crystal composition is as follows:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1
Numerical value ≤-40 93 0.117 1.598 8.5 3.6 70
Embodiment 4:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1
Numerical value ≤-40 88 0.120 1.601 12.5 3.8 63
Embodiment 5:
The formula of liquid-crystal composition is as follows:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Embodiment 6:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1
Numerical value ≤-40 96 0.101 1.599 8.9 3.5 78
Embodiment 7:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1(mpa.s)
Numerical value ≤-40 98 0.110 1.605 15.9 3.5 85
Embodiment 8:
The formula of liquid-crystal composition is as follows:
The performance parameter test result of above-mentioned liquid-crystal composition is as follows:
Project S-N(℃) Cp(℃) △n ne △ε ε⊥ γ1(mpa.s)
Numerical value ≤-40 92 0.100 1.597 8.6 3.4 92
Liquid-crystal composition obtained by eight embodiments of the above, is respectively provided with good low-temperature stability, low rotary viscosity, low Temperature area maintains the fast response time, can widen TN, the temperature in use of IPS or FFS liquid crystal modes, and ring with faster Between seasonable and wider angular field of view, TN, IPS and FFS mode operation display are highly suitable for.
Liquid-crystal composition provided by the present invention has reduction threshold voltage and the effect of response time, therefore institute of the present invention The liquid crystal media of offer be for preparing quick response, the preferable liquid crystal material of low rotary viscosity TFT LCD.
The foregoing is only presently preferred embodiments of the present invention, be not intended to limit the invention, it is all the present invention spirit and Within principle, any modification, equivalent substitution and improvements made etc. should be included in the scope of the protection.

Claims (9)

1. a kind of liquid-crystal composition of the substituted compound of polyfluoro containing methyl substituents, it is characterised in that logical including one or more Compound represented by formula I:
Wherein, R represents the alkene that alkoxy or carbon number that alkyl, carbon number that carbon number is 1-7 are 1-6 are 2-6 One or more hydrogen are formed after being replaced by fluorine in the alkyl that base, carbon number are 1-7 by 3-5 alkenyloxy group, carbon number Group, the carbon number that group, carbon number are formed after being replaced by one or more hydrogen in 1-6 alkoxy by fluorine are 3-5 Alkenyloxy group in one or more hydrogen replaced by fluorine after any one in the group that is formed;
L1, L2, L3Respective independent expression H or F;
X0Represent the alkene that haloalkyl, carbon number that alkyl, carbon number that F, Cl, carbon number are 1-6 are 1-6 are 2-6 The haloalkene that the halogenated alkoxy or carbon number that haloalkene alkyl that base, carbon number are 2-6, carbon number are 1-6 are 2-6 Any one in epoxide;
One or more in independent expression following groups:
M represents 1,2.
2. liquid-crystal composition according to claim 1, it is characterised in that the structural formula of the compound with formula I It is as follows:
3. liquid-crystal composition according to claim 1 or 2, it is characterised in that also including as represented by formula II~IV Compound:
In formula II-IV, R1-R4Alkyl that each independent expression hydrogen atom, carbon number are 1-7, carbon number are 1-6's One in the alkyl that alkenyloxy group that alkenyl that alkoxy or carbon number are 2-6, carbon number are 3-5, carbon number are 1-7 Or multiple hydrogen replaced by fluorine after formed group, carbon number for one or more hydrogen are replaced by fluorine in 1-6 alkoxy after Appointing in the group that group, the carbon number formed is formed after being replaced by one or more hydrogen in 3-5 alkenyloxy group by fluorine Meaning is a kind of;
L1-L9Respective independent expression H or F;
X1、X2Represent that haloalkyl, carbon number that alkyl, carbon number that F, Cl, carbon number are 1-6 are 1-6 are 1-6's The halogen that haloalkene alkyl that alkylene that halogenated alkoxy, carbon number are 2-6, carbon number are 2-6, carbon number are 2-6 For any one in alkenyloxy group;
Respective any one or more independent represented in following group:
Z1Represent singly-bound ,-CH2-、-CH2-CH2- ,-CH=CH- ,-C ≡ C- ,-COO- ,-OOC- ,-CF2O-、-OCH2-、- CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4- in one kind;
A, b, c, d, e, f, g represent 0,1 or 2.
4. liquid-crystal composition according to claim 3, it is characterised in that the structural formula of compound with formula II is such as Under:
Wherein, R1、R2Alkoxy or carbon that alkyl that independent expression H atom, carbon number are 1~7, carbon number are 1~6 Any one in the alkenyloxy group that alkenyl that atomicity is 2~6, carbon number are 3~5.
5. liquid-crystal composition according to claim 3, it is characterised in that the structural formula of compound with general formula III is such as Under:
Wherein, R3Represent that alkoxy or carbon number that alkyl, carbon number that H atom, carbon number are 1~7 are 1~6 are 2 ~6 alkenyl, carbon number are any one in 3~5 alkenyloxy group.
6. liquid-crystal composition according to claim 3, it is characterised in that the structural formula of compound with general formulae IV is such as Under:
Wherein, R4Represent that alkoxy or carbon number that alkyl, carbon number that H atom, carbon number are 1~7 are 1~6 are 2 ~6 alkenyl, carbon number are any one in 3~5 alkenyloxy group.
7. liquid-crystal composition according to claim 3, it is characterised in that fraction meter by weight, one or more have logical The compounds content of formula I is 1~40%, and compounds content of the one or more with formula II is 1~70%, one or more Compound with general formula III is 1~70%, and compound of the one or more with general formulae IV is 1~50%.
8. a kind of electrooptics liquid crystal display, it is characterised in that including the liquid crystal combination as any one of claim 1-7 Thing.
9. a kind of liquid-crystal composition any one of claim 1-7 is in the application of field of liquid crystal display.
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